Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes
作者:Olivier Baslé、Wilfried Raimondi、Maria del Mar Sanchez Duque、Damien Bonne、Thierry Constantieux、Jean Rodriguez
DOI:10.1021/ol102289g
日期:2010.11.19
The first organocatalytic enantio- and diastereoselective conjugate addition of α-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the
使用双官能氨基硫脲催化剂已经实现了α-酮酰胺向硝基烯烃的第一次有机催化对映体和非对映体选择性共轭加成。在这种新方法中,底物酰胺质子以高收率和高立体选择性在迈克尔反加合物的形成中起关键作用。为了说明该方法的高合成潜力,描述了通过迈克尔-迈克尔-亨利级联反应对六取代的环己烷进行非对映和对映选择性的合成。